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DOI: 10.1055/s-2006-950284
Iridium-Catalyzed Formation of Carbon-Carbon and Carbon-Heteroatom Bonds
Publication History
Publication Date:
10 October 2006 (online)
Abstract
The progress in catalytic organic synthesis with iridium was far behind that with rhodium or palladium in the early 1990s. However, many useful reactions have recently been reported, and iridium catalysts have now been recognized to be useful in organic synthesis. This review covers iridium-catalyzed carbon-carbon and carbon-heteroatom bond formation with particular emphasis on useful reactions for organic synthesis.
1 Introduction
2 Allylic Substitution
2.1 Allylic Alkylation
2.2 Allylic Amination
2.3 Allylic Etherification
3 Reaction of Alkynes
3.1 Cyclotrimerization of Alkynes
3.2 Cycloaddition of Enynes
3.3 Cycloisomerization of Enynes
3.4 Dimerization
3.5 Alkynylation
4 Alkylation with Alcohols
4.1 N-Alkylation
4.2 C-Alkylation
5 Aldol and Related Reactions
6 Carbonylation
7 Miscellaneous Reactions
8 Conclusion
Key words
iridium - asymmetric catalysis - allylations - alkynes - aldol reactions
- 1
Vaska L. Acc. Chem. Res. 1968, 1: 335 - 2
Atwood JD. Coord. Chem. Rev. 1988, 83: 93 - 3
Crabtree RH.Felkin H.Morris GE. J. Organomet. Chem. 1977, 141: 205 - 4
Crabtree RH. Acc. Chem. Res. 1979, 12: 331 - 5
Stork G.Kahne DE. J. Am. Chem. Soc. 1983, 105: 1072 - 6
Lightfoot A.Schnider P.Pfaltz A. Angew. Chem. Int. Ed. 1998, 37: 2897 - 7
Pfaltz A.Blankenstein J.Hilgraf R.Hörmann E.McIntyre S.Menges F.Schönleber M.Smidt SP.Wüstenberg B.Zimmermann N. Adv. Synth. Catal. 2003, 345: 33 - 8
Bell S.Wüstenberg B.Kaiser S.Menges F.Netscher T.Pfaltz A. Science 2006, 311: 642 - 9
Cui X.Burgess K. Chem. Rev. 2005, 105: 3272 - 10
Takeuchi R. Synlett 2002, 1954 - 11
Ishii Y.Sakaguchi S. Bull. Chem. Soc. Jpn. 2004, 77: 909 - 12
Fujita K.Yamaguchi R. Synlett 2005, 560 - 13
Chini P.Martinengo S. Inorg. Chem. 1967, 6: 837 - 14
Tjaden EB.Stryker JM. J. Am. Chem. Soc. 1990, 112: 6420 - 15
Tsuji J. Palladium Reagents and Catalysts: New Perspective for the 21st Century Wiley; West Sussex: 2004. p.431 - Recently, Pd-catalyzed branched-product-selective allylic substitution has been reported; see:
-
16a
Prétôt R.Pfaltz A. Angew. Chem. Int. Ed. 1998, 37: 323 -
16b
You S.-L.Zhu X.-Z.Luo Y.-M.Hou X.-L.Dai L.-X. J. Am. Chem. Soc. 2001, 123: 7471 - 17
Takeuchi R.Kashio M. Angew. Chem., Int. Ed. Engl. 1997, 36: 263 - 18
Takeuchi R.Kashio M. J. Am. Chem. Soc. 1998, 120: 8647 - 19
Takeuchi R. Polyhedron 2000, 19: 557 - 20
Janssen JP.Helmchen G. Tetrahedron Lett. 1997, 38: 8025 - 21
García-Yebra C.Janssen JP.Rominger F.Helmchen G. Organometallics 2004, 23: 5459 - 22
Feringa BL. Acc. Chem. Res. 2000, 33: 346 - 23
Bartels B.Helmchen G. Chem. Commun. 1999, 741 - 24
Bartels B.García-Yebra C.Rominger F.Helmchen G. Eur. J. Inorg. Chem. 2002, 2569 - 25
Bartels B.García-Yebra C.Helmchen G. Eur. J. Org. Chem. 2003, 1097 - 26
Lipowsky G.Miller N.Helmchen G. Angew. Chem. Int. Ed. 2004, 43: 4595 - 27
Alexakis A.Polet D. Org. Lett. 2004, 6: 3529 - 28
Polet D.Alexakis A. Org. Lett. 2005, 7: 1621 - 29
Polet D.Alexakis A.Tissot-Croset K.Corminboeuf C.Ditrich K. Chem. Eur. J. 2006, 12: 3596 - 30
Fuji K.Kinoshita N.Tanaka K.Kawabata T. Chem. Commun. 1999, 2289 - 31
Kinoshita N.Marx KH.Tanaka K.Tsubaki K.Kawabata T.Yoshikai N.Nakamura E.Fuji K. J. Org. Chem. 2004, 69: 7960 - 32
Kanayama T.Yoshida K.Miyabe H.Takemoto Y. Angew. Chem. Int. Ed. 2003, 42: 2054 - 33
Kanayama T.Yoshida K.Miyabe H.Kimachi T.Takemoto Y. J. Org. Chem. 2003, 68: 6197 - 34
Takeuchi R.Tanabe K. Angew. Chem. Int. Ed. 2000, 39: 1975 - 35
Kezuka S.Kanemoto K.Takeuchi R. Tetrahedron Lett. 2004, 45: 6403 - 36
Graening T.Hartwig JF. J. Am. Chem. Soc. 2005, 127: 17192 - 37
Masuyama Y.Chiyo T.Kurusu Y. Synlett 2005, 2251 - 38
Johansen M.Jørgensen KA. Chem. Rev. 1998, 98: 1689 - 39
Takeuchi R.Ue N.Tanebe K.Yamashita K.Shiga N. J. Am. Chem. Soc. 2001, 123: 9525 - 40
Takeuchi R.Shiga N. Org. Lett. 1999, 1: 265 - 41
Trost BM.Keinan E. J. Org. Chem. 1979, 44: 3451 - 42
Kazmaier U.Zumpe FL. Angew. Chem. Int. Ed. 2000, 39: 802 - 43
Hutzinger MW.Oehlschalager AC. J. Org. Chem. 1991, 56: 2918 - 44
de Vries AHM.Meetsma A.Feringa BL. Angew. Chem., Int. Ed. Engl. 1996, 35: 2374 - 45
Ohmura T.Hartwig JF. J. Am. Chem. Soc. 2002, 124: 15164 - 46
Kiener CA.Shu C.Incarvito C.Hartwig JF. J. Am. Chem. Soc. 2003, 125: 14272 - 47
Shu C.Leitner A.Hartwig JF. Angew. Chem. Int. Ed. 2004, 43: 4797 - 48
Leitner A.Shu C.Hartwig JF. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5830 - 49
Leitner A.Shu C.Hartwig JF. Org. Lett. 2005, 7: 1093 - 50
Leitner A.Shekhar S.Pouy MJ.Hartwig JF. J. Am. Chem. Soc. 2005, 127: 15506 - 51
Tissot-Croset K.Polet D.Alexakis A. Angew. Chem. Int. Ed. 2004, 43: 2426 - 52
Desimoni G.Faita G.Quadrelli P. Chem. Rev. 2003, 103: 3119 - 53
Miyabe H.Matsumura A.Moriyama K.Takemoto Y. Org. Lett. 2004, 6: 4631 - 54
Lipowsky G.Helmchen G. Chem. Commun. 2004, 116 - 55
Welter C.Koch O.Lipowsky G.Helmchen G. Chem. Commun. 2004, 896 - 56
Miyabe H.Yoshida K.Kobayashi Y.Matsumura A.Takemoto Y. Synlett 2003, 1031 - 57
Welter C.Dahnz A.Brunner B.Streiff S.Dübon P.Helmchen G. Org. Lett. 2005, 7: 1239 - 58
Weihofen R.Dahnz A.Tverskoy O.Helmchen G. Chem. Commun. 2005, 3541 - 59
Matunas R.Lai AJ.Lee C. Tetrahedron 2005, 61: 6298 - 60
Keinan E.Sahai M.Roth Z.Nudelman A.Herzig J. J. Org. Chem. 1985, 50: 3558 - 61
López F.Ohmura T.Hartwig JF. J. Am. Chem. Soc. 2003, 125: 3426 - 62
Shu C.Hartwig JF. Angew. Chem. Int. Ed. 2004, 43: 4794 - 63
Roberts JP.Lee C. Org. Lett. 2005, 7: 2679 - 64
Miyabe H.Yoshida K.Matsumura A.Yamauchi M.Takemoto Y. Synlett 2003, 567 - 65
Miyabe H.Yoshida K.Matsumura A.Yamauchi M.Takemoto Y. J. Org. Chem. 2005, 70: 2148 - 66
Miyabe H.Matsumura A.Yoshida K.Yamauchi M.Takemoto Y. Synlett 2004, 2123 - 67
Fischer C.Defieber C.Suzuki T.Carreira EM. J. Am. Chem. Soc. 2004, 126: 1628 - 68
Saito S.Yamamoto Y. Chem. Rev. 2000, 100: 2901 - 69
Callman JP.Kang JW.Little WF.Sullivan MF. Inorg. Chem. 1968, 7: 1298 - 70
Takeuchi R.Tanaka S.Nakaya Y. Tetrahedron Lett. 2001, 42: 2991 - 71
Kezuka S.Tanaka S.Ohe T.Nakaya Y.Takeuchi R. J. Org. Chem. 2006, 71: 543 - 72
Yamamoto Y.Arakawa T.Ogawa R.Itoh K. J. Am. Chem. Soc. 2003, 125: 12143 - 73
McDonald FE.Zhu HY.Holmquist CR. J. Am. Chem. Soc. 1995, 117: 6605 - 74
Witulski B.Stengel T.Fernández-Hernández JM. Chem. Commun. 2000, 1965 - 75
Vollhardt KPC. Angew. Chem., Int. Ed. Engl. 1984, 23: 539 - 76
Dufková L.Císařová I.Štepnička P.Kotra M. Eur. J. Org. Chem. 2003, 2882 - 77
Shibata T.Fujimoto T.Yokota K.Takagi K. J. Am. Chem. Soc. 2004, 126: 8382 - 78
Fabbian M.Marsich N.Farnetti E. Inorg. Chim. Acta 2004, 357: 2881 - 79
Farnetti E.Marsich N. J. Organomet. Chem. 2004, 689: 14 - 80
Takeuchi R.Nakaya Y. Org. Lett. 2003, 5: 3659 - 81
Kezuka S.Okado T.Niou E.Takeuchi R. Org. Lett. 2005, 7: 1711 - 82
Shibata T.Takasaku K.Takesue Y.Hirata N.Takagi K. Synlett 2002, 1681 - 83
Aubert C.Buisine O.Malacria M. Chem. Rev. 2002, 102: 813 - 84
Chatani N.Inoue H.Morimoto T.Muto T.Murai S. J. Org. Chem. 2001, 66: 4433 - 85
Yamamoto Y.Hayashi H.Saigoku T.Nishiyama H. J. Am. Chem. Soc. 2005, 127: 10804 - 86
Shibata T.Yamasaki M.Kadowaki S.Takagi K. Synlett 2004, 2812 - 87
Shibata T.Kobayashi Y.Maekawa S.Toshida N.Takagi K. Tetrahedron 2005, 38: 9018 - 88
Ohmura T.Yorozuya S.Yamamoto Y.Miyaura N. Organometallics 2000, 19: 365 - 89
Jun C.-H.Crabtree RH. Tetrahedron Lett. 1992, 33: 7119 - 90
Hirabayashi T.Sakaguchi S.Ishii Y. Adv. Synth. Catal. 2005, 347: 872 - 91
Fischer C.Carreira EM. Org. Lett. 2001, 3: 4319 - 92
Fischer C.Carreira EM. Synthesis 2004, 1497 - 93
Sakaguchi S.Mizuta T.Furuwan M.Kubo T.Ishii Y. Chem. Commun. 2004, 1638 - 94
Sakaguchi S.Kubo T.Ishii Y. J. Org. Chem. 2001, 66: 4710 - 95
Fujita K.Li Z.Ozeki N.Yamaguchi R. Tetrahedron Lett. 2003, 44: 2687 - 96
Fujita K.Yamamoto K.Yamaguchi R. Org. Lett. 2002, 4: 2691 - 97
Fujita K.Fujii T.Yamaguchi R. Org. Lett. 2004, 6: 3525 - 98
Taguchi K.Nakagawa H.Hirabayashi T.Sakaguchi S.Ishii Y. J. Am. Chem. Soc. 2004, 126: 72 - 99
Matsuda I.Hasegawa Y.Makino T.Itoh K. Tetrahedron Lett. 2000, 41: 1405 - 100
Matsuda I.Makino T.Hasegawa Y.Itoh K. Tetrahedron Lett. 2000, 41: 1409 - 101
Matsuda I.Komori K.Itoh K. J. Am. Chem. Soc. 2002, 124: 9072 - 102
Zhao C.-X.Duffey MO.Taylor SJ.Morken JP. Org. Lett. 2001, 3: 1829 - 103
Townes JA.Evans MA.Queffelec J.Taylor SJ.Morken JP. Org. Lett. 2002, 4: 2537 - 104
Shibata T.Takagi K. J. Am. Chem. Soc. 2000, 122: 9852 - 105
Shibata T.Toshida N.Yamasaki M.Maekawa S.Takagi K. Tetrahedron 2005, 61: 9974 - 106
Shibata T.Yamashita K.Katayama E.Takagi K. Tetrahedron 2002, 58: 8661 - 107
Shibata T.Yamashita K.Ishida H.Takagi K. Org. Lett. 2001, 3: 1217 - 108
Shibata T.Kadowaki S.Hirase M.Takagi K. Synlett 2003, 573 - 109
Murai S.Sonoda N. Angew. Chem., Int. Ed. Engl. 1979, 18: 837 - 110
Chatani N.Ikeda S.-I.Ohe K.Murai S. J. Am. Chem. Soc. 1992, 114: 9710 - 111
Kownacki I.Marciniec B.Szubert K.Kubicki M. Organometallics 2005, 24: 6179 - 112
Chatani N.Yamaguchi S.Fukumoto Y.Murai S. Organometallics 1995, 14: 4418 - 113
Murakami M.Itami K.Ubukata M.Tsuji I.Ito Y. J. Org. Chem. 1998, 63: 4 - 114
Takeuchi R.Akiyama Y. J. Organomet. Chem. 2002, 651: 137 - 115
Sunley GJ.Watson DJ. Catal. Today 2000, 58: 293 - 116
Jones JH. Platinum Met. Rev. 2000, 44: 94 - 117
Haynes A.Maitlis PM.Morris GE.Sunley GJ.Adams H.Badger PW.Bowers CM.Cook DB.Elliot PIP.Ghaffar T.Green H.Griffin TR.Payne M.Pearson JM.Taylor MJ.Vickers PW.Watt RJ. J. Am. Chem. Soc. 2004, 126: 2847 - 118
Takaya H.Naota T.Murahashi S.-I. J. Am. Chem. Soc. 1998, 120: 4244 - 119
Murahashi S.-I.Takaya H. Acc. Chem. Res. 2000, 33: 225 - 120
Okimoto Y.Sakaguchi S.Ishii Y. J. Am. Chem. Soc. 2002, 124: 1590 - 121
Yasukawa T.Satoh T.Miura M.Nomura M. J. Am. Chem. Soc. 2002, 124: 12680 - 122
Koike T.Du X.Sanada T.Danda Y.Mori A. Angew. Chem. Int. Ed. 2003, 42: 89 - 123
Fujita K.Nonogawa M.Yamaguchi R. Chem. Commun. 2004, 1926